Abstract
Abstract The cis-trans ratio of the alkenes formed in Wittig reactions of semistabilised ylides (derived from benzyltriarylphosphonium salts in ethanolic sodium ethoxide) with benz-aldehyde, acetaldehyde or trimethylacetaldehyde increases as steric crowding at phos-phorus increases. In contrast, the cis-trans ratio of the unsaturated esters formed in the related reactions of the stabilised ethoxycarbonylmethylene ylides decreases as steric crowding at phosphorus increases. The relevance of these results to recent proposals for the mechanism of the Wittig reaction is considered.
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